GB1007777A - Improvements in or relating to hendecapeptides - Google Patents

Improvements in or relating to hendecapeptides

Info

Publication number
GB1007777A
GB1007777A GB24980/62A GB2498062A GB1007777A GB 1007777 A GB1007777 A GB 1007777A GB 24980/62 A GB24980/62 A GB 24980/62A GB 2498062 A GB2498062 A GB 2498062A GB 1007777 A GB1007777 A GB 1007777A
Authority
GB
United Kingdom
Prior art keywords
methyl ester
lysine
seryl
glycyl
ester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB24980/62A
Inventor
Roger Boissonnas
Edmond Sandrin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz Patent Ltd
Sandoz AG
Original Assignee
Sandoz Patent Ltd
Sandoz AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz Patent Ltd, Sandoz AG filed Critical Sandoz Patent Ltd
Publication of GB1007777A publication Critical patent/GB1007777A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/16—Oxytocins; Vasopressins; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • A61K38/095—Oxytocins; Vasopressins; Related peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/22—Tachykinins, e.g. Eledoisins, Substance P; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention comprises the hendecapeptide pyroglutamyl - prolyl - seryl - lysyl - aspartyl alanyl - phenylalanyl - isoleucyl - glycyl leucyl-methionine amide (wherein all the amino acid residues are of L-configuration), its acid addition salts, and peptide having a protective group on the e -amino radical of the lysine residue and, optionally, a protective group on the end amido group of the pyroglutamine residue and/or a protective group on the b -carboxyl radical of the aspartic acid residue, and the preparation thereof by condensing a suitably protected pyroglutamyl-prolyl-seryl-lysine having, optionally, the carboxyl radical of the lysine residue substituted with a radical reactive with amino radicals to form an amide link with aspartyl-alaryl - phenylalanyl - isoleucyl - glycyl - leucyl-methionine amide, optionally protected, and if desired removing the protecting groups in one or more stages. Protecting groups for the pyroglutamyl residue are, for example, carbobenzoxy, carbo-tertiary-butoxy and p-nitrocarbo benzoxy; for the Ne amino group of lysine, the aforementioned together with phthalyl and formyl; and for the b -carboxyl group benzoyl, p-nitrobenzyl, methyl, ethyl, tertiary-butyl and amido radicals. Groups in the tetrapeptide reactive with amino radicals to form amide linkages are azide, and p-nitrophenyl ester radicals; an asymmetric anhydride of the detetrapept or the reaction product of the tetrapeptide with dicyclohexylcarbodiimide. Pyroglutamyl - prolyl - seryl - (Ne - carbotertiary-butoxy) lysine hydrazide is prepared by condensing carbobenzoxypyroglutamine p-nitrophenyl ester with prolin to give carbobenzoxypyroglutamyl-proline, condensing this with seryl - Ne - carbobenzoxylysine methyl ester to give carbobenzoxypyroglutamyl - prolyl - seryl-lysine methyl ester, hydrogenating this to give the free tetra peptide ester, forming the Ne -carbo - t - butoxy - lysine derivative and reacting the ester with hydrazine. Seryl - Ne - carbobenzoxylysine methyl ester is prepared by condensing N-tritylserine with Ne -carbobenzoxylysine methyl ester and detritylating the protected dipeptide. Aspartyl - alanyl - phenylalanyl - isoleucyl-glycyl - leucyl - methioninamide is prepared from carbobenzoxyphenylalamine p-nitrophenyl ester and isoleucine methyl ester through carbo-benzoxyphenylalanyl - isoleucyl methyl ester, carbobenzoxy - o - benzyloxyaspartyl - isoleucine methyl ester, carbo - tert - butoxy - aspartyl-alanyl - phenylalanyl - isoleucine methyl ester and its hydrazide and carbo-tert-butyoxy-aspartyl - alanyl - phenylalanyl - isoleucyl - glycyl - leucyl - methioninamide, by stepwise addition of an amino acid with liberation of the free amino peptides, the last stage being condensation between a tetra- and a tri-peptide. Glycyl - leucyl - methioninamide is prepared from trityl - glycyl - leucine and methionine amide through the trityl tripeptamide. Pharmaceutical compositions showing hypotensive activity comprise the compounds of the invention with an inert pharmaceutical carrier. Specifications 872,332 and 878,732 are referred to.
GB24980/62A 1961-07-14 1962-06-29 Improvements in or relating to hendecapeptides Expired GB1007777A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH826461A CH420187A (en) 1961-07-14 1961-07-14 Process for the production of a previously unknown polypeptide

Publications (1)

Publication Number Publication Date
GB1007777A true GB1007777A (en) 1965-10-22

Family

ID=4337671

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24980/62A Expired GB1007777A (en) 1961-07-14 1962-06-29 Improvements in or relating to hendecapeptides

Country Status (7)

Country Link
US (2) US3309353A (en)
AT (1) AT258483B (en)
CH (1) CH420187A (en)
ES (2) ES279196A1 (en)
FR (2) FR2094M (en)
GB (1) GB1007777A (en)
OA (1) OA01249A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT251777B (en) * 1961-10-05 1967-01-25 Farmaceutici Italia Process for the preparation of new hendekapeptides
GB1054191A (en) * 1963-03-01
NL6501206A (en) * 1964-02-12 1965-08-13
DE1518349C3 (en) * 1965-09-21 1975-03-20 Schering Ag, 1000 Berlin Und 4619 Bergkamen Process for the preparation of eledoisin-active compounds
US3972860A (en) * 1969-09-02 1976-08-03 Moriarty Carole L L-aspartyl-L-phenylglycine esters of lower alkanols
GB1492640A (en) * 1975-07-08 1977-11-23 Ucb Sa L-pyroglutamyl-l-prolinamide
JPS59112984A (en) * 1982-12-21 1984-06-29 Shionogi & Co Ltd 1,4-benzodiazepine derivative

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2953558A (en) * 1956-11-02 1960-09-20 Monsanto Chemicals Heteropolypeptide
US3093627A (en) * 1958-07-03 1963-06-11 Ciba Geigy Corp Polypeptides and process for their manufacture
US2987442A (en) * 1959-02-17 1961-06-06 Smith Kline French Lab Method of treating hypertension with [2-(2, 6-dimethylphenoxy)-propyl]-trimethyl ammonium salts
US2986573A (en) * 1961-01-18 1961-05-30 Schering Corp Method for the treatment of hypertension

Also Published As

Publication number Publication date
AT258483B (en) 1967-11-27
CH420187A (en) 1966-09-15
ES279196A1 (en) 1963-05-01
OA01249A (en) 1969-01-25
FR2012M (en) 1963-09-09
FR2094M (en) 1963-10-21
ES279197A1 (en) 1963-04-16
US3299035A (en) 1967-01-17
US3309353A (en) 1967-03-14

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